(R)-tetramethyl [2,2'-didodecyloxy-6,6'-[1,1'-binaphthylbis(methylene)]]bis-phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-tetramethyl [2,2'-didodecyloxy-6,6'-[1,1'-binaphthylbis(methylene)]]bis-phosphonate
• 英文别名: [1,1'-Bi[2-(dodecyloxy)naphthalene]-6,6'-diylbismethylene]bis(phosphonic acid dimethyl) ester；6-(dimethoxyphosphorylmethyl)-1-[6-(dimethoxyphosphorylmethyl)-2-dodecoxynaphthalen-1-yl]-2-dodecoxynaphthalene
• 化学式: C₅₀H₇₆O₈P₂
• 分子量: 867.096
• InChiKey: HEKWEUOHBWWCBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  60
• 可旋转键数：
  33
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-tetramethyl [2,2'-didodecyloxy-6,6'-[1,1'-binaphthylbis(methylene)]]bis-phosphonate 、 3,5-bis{2'[3,5-bis[2'-(4-dibutylaminophenyl)vinyl]]}benzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以71%的产率得到
  参考文献：
  名称：

  Synthesis and Photoluminescent Properties of 1,1‘-Binaphthyl-Based Chiral Phenylenevinylene Dendrimers

  摘要：

  New chiral, soluble binaphthyl derivatives that incorporate stilbenoid dendrons at the 6,6'-positions have been prepared. The synthesis of the new enantiopure dendrimers was performed in a convergent manner by Horner-Wadsworth-Emmons (HWE) reaction of the appropriately functionalized 1,1'-binaphthyl derivative (R)-1 and the appropriate dendrons (R)(2n)G(n)-CHO. Different electroactive units were incorporated in the peripheral positions of the dendrons in order to tune both the optical and electrochemical behavior of these systems. Fluorescence measurements on the chiral dendrimers reveal a strong emission with maxima between 409 and 508 nm depending upon the substitution pattern. Finally, the redox properties of the dendrimers were determined by cyclic voltammetry, showing the influence of the functional groups at the peripheral positions of the dendrimer on the redox behavior of these systems.

  DOI：

  10.1021/jo026222s
• 作为产物：
  描述：

  (R)-2,2'-di(dodecyloxy)-6,6'-diformyl-1,1'-binaphthalene 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 四乙基溴化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (R)-tetramethyl [2,2'-didodecyloxy-6,6'-[1,1'-binaphthylbis(methylene)]]bis-phosphonate
  参考文献：
  名称：

  新的手性联萘基结构单元：合成第一个光学活性四硫富瓦烯和11,11,12,12-四氰基-9，10-蒽醌二甲烷二聚体

  摘要：

  已经合成了带有三苯基膦或膦酸酯基团的新对映体纯的联萘衍生物，并将其用作制备第一个光学活性TTF和TCAQ二聚体的基础材料。由于两个萘环的旋转受限制，联萘衍生物是寻找具有增强尺寸的材料时理想的候选物，可用作电活性单元之间的非平面间隔基。电活性单元与萘片段共轭的二聚体的电子吸收光谱揭示了分子内光致电子转移过程的存在，该过程是在5和6中从TTF到萘单元，以及在7中从萘部分到TCAQ单元。 。

  DOI：

  10.1021/jo0009649

文献信息

• New Chiral Binaphthyl Building Blocks:  Synthesis of the First Optically Active Tetrathiafulvalene and 11,11,12,12-Tetracyano-9,10-anthraquinodimethane Dimers
  作者：Rafael Gómez、José L. Segura、Nazario Martín

  DOI：10.1021/jo0009649

  日期：2000.11.1

  rotation of the two naphthalene rings, binaphthyl derivatives are ideal candidates to be used as nonplanar spacers between electroactive units in the search for materials with enhanced dimensionality. The electronic absorption spectra of dimers in which the electroactive unit is in conjugation with the naphthalene fragment reveal the presence of intramolecular photoinduced electron-transfer process from

  已经合成了带有三苯基膦或膦酸酯基团的新对映体纯的联萘衍生物，并将其用作制备第一个光学活性TTF和TCAQ二聚体的基础材料。由于两个萘环的旋转受限制，联萘衍生物是寻找具有增强尺寸的材料时理想的候选物，可用作电活性单元之间的非平面间隔基。电活性单元与萘片段共轭的二聚体的电子吸收光谱揭示了分子内光致电子转移过程的存在，该过程是在5和6中从TTF到萘单元，以及在7中从萘部分到TCAQ单元。 。
• Synthesis and Photoluminescent Properties of 1,1‘-Binaphthyl-Based Chiral Phenylenevinylene Dendrimers
  作者：Enrique Díez-Barra、Joaquín C. García-Martínez、Riánsares del Rey、Julián Rodríguez-López、Francesco Giacalone、José L. Segura、Nazario Martín

  DOI：10.1021/jo026222s

  日期：2003.4.1

  New chiral, soluble binaphthyl derivatives that incorporate stilbenoid dendrons at the 6,6'-positions have been prepared. The synthesis of the new enantiopure dendrimers was performed in a convergent manner by Horner-Wadsworth-Emmons (HWE) reaction of the appropriately functionalized 1,1'-binaphthyl derivative (R)-1 and the appropriate dendrons (R)(2n)G(n)-CHO. Different electroactive units were incorporated in the peripheral positions of the dendrons in order to tune both the optical and electrochemical behavior of these systems. Fluorescence measurements on the chiral dendrimers reveal a strong emission with maxima between 409 and 508 nm depending upon the substitution pattern. Finally, the redox properties of the dendrimers were determined by cyclic voltammetry, showing the influence of the functional groups at the peripheral positions of the dendrimer on the redox behavior of these systems.